Enantioselective synthesis of α-methylene-γ-butyrolactones using chiral Pd(II)-SPRIX catalyst

Tetrahedron Letters

Volumn 44, Issue 28, 2003, Pages 5201-5204

  Muthiah, Chinnasamy ^a   Arai, Midori A ^a   Shinohara, Toshio ^a   Arai, Takayoshi ^a   Takizawa, Shinobu ^a   Sasai, Hiroaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA BUTYROLACTONE DERIVATIVE; PALLADIUM COMPLEX;

ARTICLE; CATALYST; CHIRALITY; CYCLIZATION; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SYNTHESIS;

EID: 0038345989     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01250-4     Document Type: Article

References (35)

1. Trost B.M., van Vranken D.L. Chem. Rev. 96:1996;395-422.
2. Hayashi T. J. Organomet. Chem. 576:1999;195-202.
3. Tsuji J. Palladium Reagents and Catalysts, Innovaions in Organic Synthesis. 1995;19-124 John Wiley & Sons, Chichester, UK.
4. Tenaglia A., Heumann A. Angew. Chem., Int. Ed. 38:1999;2180-2184. and references cited therein.
5. Hosokawa T., Murahashi S.-I. Acc. Chem. Res. 23:1990;49-54.
6. Sodeoka M., Ohrai K., Shibasaki M. J. Org. Chem. 60:1995;2648-2649.
7. Shibasaki M., Boden C.D.J., Kojima A. Tetrahedron. 53:1997;7371-7395.
8. Uozumi Y., Kato K., Hayashi T. J. Am. Chem. Soc. 119:1997;5063-5064.
9. Hollis T.K., Overman L.E. J. Organomet. Chem. 576:1999;290-299.
10. Hatano M., Terada M., Mikami K. Angew. Chem., Int. Ed. 40:2001;249-253. and references cited therein.
11. Kato K., Yamamoto Y., Akita H. Tetrahedron Lett. 43:2002;4915-4917.
12. Zhang Q., Lu X. J. Am. Chem. Soc. 122:2000;7604-7605.
13. Zhang Q., Lu X., Han X. J. Org. Chem. 66:2001;7676-7684. and references cited therein.
14. Zhu G., Lu X. J. Org. Chem. 60:1995;1087-1089.
15. Zhu G., Lu X. Tetrahedron: Asymmetry. 6:1995;885-892.
16. Lu X., Zhu G., Wang Z. Synlett. 1998;115-121. and references cited therein.
17. Lei A., He M., Zhang X. J. Am. Chem. Soc. 124:2002;8198-8199. and references cited therein.
18. Lee K.H., Huang E.-S., Piantodosi C., Pagani J., Geissman T.A. Cancer Res. 31:1971;1649-1654.
19. Gammil R.B., Wilson C.A., Bryson T.A. Synth. Commun. 5:1975;245-268.
20. Mori K. Tetrahedron. 39:1983;3107-3109.
21. Yoshikawa M., Shimoda H., Uemura T., Morikawa T., Kawahara Y., Matsuda H. Bioorg. Med. Chem. 2000;2071-2077.
22. Ma S., Lu X. J. Org. Chem. 56:1991;5120-5125.
23. Sturla S.J., Buchwald S.L. J. Org. Chem. 64:1999;5547-5550.
24. Hiroi K., Watanabe T., Kawagishi R., Abe I. Tetrahedron Lett. 41:2000;891-895.
25. Jeong N., Sung B.K., Choi Y.K. J. Am. Chem. Soc. 122:2000;6771-6772.
26. Shibata T., Takagi K. J. Am. Chem. Soc. 122:2000;9852-9853.
27. Kang S.-K., Kim K.-J., Hong Y.-T. Angew. Chem., Int. Ed. 41:2002;1584-1586.
28. Asao N., Nogami T., Takahashi K., Yamamoto Y. J. Am. Chem. Soc. 124:2002;764-765.
29. Arai M.A., Arai T., Sasai H. Org. Lett. 1:1999;1795-1797.
30. Arai M.A., Kuraishi M., Arai T., Sasai H. J. Am. Chem. Soc. 123:2001;2907-2908.
31. Shinohara T., Wakita K., Arai M.A., Arai T., Sasai H. Tetrahedron Lett. 44:2003;711-714.
32. 3.
33. 2Pd (55%, 46% ee).
34. Shinohara T., Wakita K., Arai M.A., Arai T., Sasai H. Heterocycles. 59:2003;587-593.
35. 5 237.0739. Found 237.0767.